(2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester

Base Information

• Chemical Name: (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester
• CAS No.: 174623-95-1
• Molecular Formula: C₃₀H₄₉NO₈
• Molecular Weight: 551.721
• Mol file: 174623-95-1.mol

Synonyms:(2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester

Chemical Property of (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester

There total 26 articles about (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S,3R)-(R)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl-3-{[(3R,4S)-4-{[(benzyloxy)carbonyl](methyl)amino}-3-(methoxymethoxy)-5-phenylpentanoyl]oxy}-2-methyldecanoate (174623-94-0) → (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester (174623-95-1)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In ethyl acetate; for 5h;

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester (174623-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NaHCO₃ / dimethylformamide

2: 82 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / 6 h / 20 °C

3: 87 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

4: H₂ / Pd(OH)2

With dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium dihydroxide; In dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Esterification / 3: Deacylation / 4: Hydrogenolysis;

DOI:10.1055/s-1999-2765

Reference yield:

(S)-2-hydroxy-3-methylbutyric acid benzyl ester (65138-05-8) → (2S,3R)-3-((3R,4S)-3-Methoxymethoxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester (174623-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / 6 h / 20 °C

2: 87 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

3: H₂ / Pd(OH)2

With dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen; triethylamine; trifluoroacetic acid; palladium dihydroxide; In dichloromethane; 1: Esterification / 2: Deacylation / 3: Hydrogenolysis;

DOI:10.1055/s-1999-2765

upstream raw materials:

(2S,3R)-(R)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl-3-{[(3R,4S)-4-{[(benzyloxy)carbonyl](methyl)amino}-3-(methoxymethoxy)-5-phenylpentanoyl]oxy}-2-methyldecanoate

(S)-2-Hydroxy-3-methylbutanoic acid

n-heptyllithium

(S)-2-hydroxy-3-methylbutyric acid benzyl ester

Downstream raw materials:

(-)-hapalosin

(2S,5S,6R,10R,11S)-5-Benzyl-10-heptyl-2-isopropyl-6-methoxymethoxy-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione